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WARNING: Only spoilers from the current season (Season 5) are whited out.
- A Father to His Men: Reddington makes it especially clear that if anyone hurts anyone who works for him, they will die.
- Beneath Suspicion: Many of Reddington's associates lead very innocuous lives. Such as a suburban mother as a counterfeiter.
- Bunny-Ears Lawyer: Many of the people under Reddington have very unusual quirks.
- Undying Loyalty: Many of Reddington's associates wouldn't hesitate to fight to their last breath to protect him.
"Mr." Kate Kaplan/Kathryn Nemec
Played By: Susan BlommaertReddington's personal "cleaner" that comes in to scrub crime scenes.
- Arc Villain: Starts to be the bad guy in "Dembe Zuma" after she nearly died.
- Butch Lesbian: Her sexuality is offhandedly referred to in "Dr. James Covington".
- Lipstick Lesbian: Moreso in her youth.
- Clean Up Crew: She works as a professional cleaner for Reddington, disposing of any inconvenient dead bodies. Liz has even started to use her.
- Consummate Professional: Kaplan is very calm and professional as "he" goes about "his" work.
- Cool Old Lady/Samus Is a Girl: "Mr." Kaplan is actually a woman.
- Even Evil Has Standards: Deceived Red in order to ensure the safety of Liz and her baby..
- From Nobody to Nightmare: Mr. Kaplan was a simple nanny named Kathryn Nemec who took care of a young Masha Rostova (Liz Keen). Unfortunately, she got caught up in the antics of Katerina Rostova and Raymond Reddington, and her whole life got blown up. When she tried to live a simple life, her wife was killed by a criminal. She was shot in the head, while earning the nickname "Mr. Kaplan". After, she went to Red to work for him as his cleaner, on the terms that she will always choose Liz over him. Doing so led to her being shot again, and now she is on the warpath against his organization.
- The Lost Lenore: Her girlfriend, Annie Kaplan, was shot to death, and Mr. Kaplan was unable to save her.
- A Mother to Her Men: When her crew of "cleaners" is killed in Mr Gregory Devry, she is devastated.
- No Good Deed Goes Unpunished: Red shoots her after he fully realized that she did help Liz escape on purpose.
- Only Known by Their Nickname: Her real name is Kathryn Nemec. Her nickname comes from her dead girlfriend, Annie Kaplan, when her killer mockingly referred to Kathryn as 'Mr. Kaplan.'
- Put on a Bus: Hasn't been seen after the events of "Alexander Kirk", but there's a mention of her in "The Harem". After recovering from her gunshot wound she disappears again for several episodes, returning in "Dembe Zuma".
- Revolvers Are Just Better: Uses one in "Leonard Caul" to take out a couple of assassins masquerading as FBI agents.
- Uses it in "Mr. Kaplan" to shoot at Baz. She tells Raymond that she didn't want to use it on him if she could.
- Spanner in the Works: Since she turns against Reddington, she's one of the few enemies who can bring Red into trouble.
- Thanatos Gambit: She gives Tom a suitcase with a skeleton inside to give to Liz and shoots herself as part of a plan to basically destroy Reddington's empire.
- Undying Loyalty: To Reddington. In "Leonard Caul" when Reddington is seriously wounded and the Cabal's forces are closing in he practically has to force her to flee.
- Requiem reveals her true undying loyalty is to Liz, as she tells Red in a flashback that she will always choose Liz over him if she has to.
Played By: Deborah S. CraigReddington's personal aide and presumed to be the one in charge of handling his finances. She's wanted by law enforcement agencies worldwide for financial crimes tied with Reddington.
- Boom, Headshot: Unceremoniously executed by Anslo Garrick.
- Does Not Like Men: According to Reddington. She does seem to like him, though. Beyond that comment this really more of an Informed Attribute.
- Evil Genius: For Reddington.
- Sacrificial Lion: When Anslo Garrick kills her in Episode 9 (very nearly followed by Dembe' in the closing seconds), it very effectively destroys Plot Armour and displays Garrick's level of villainy and threat. Crosses over with Sacrificial Lamb, as she was a recurring character only - the next two-parter that season, which is the Season Finale, demonstrated this even stronger with Berlin's killing of Meera Malik (in very similar circumstances); Luli was intended to demonstrate, for the first time, just how dangerous a high-numbered name on the blacklist (which the Task Force hadn't faced before then) can really be.
- The Smart Girl: She received her PhD in Economics from Stanford University and did head the SAL Capital Group before she was arrested in 2002/06 of insider trading via wire and securities fraud.
- The Stoic: She does not display many emotions until the time of her death.
- Unholy Matrimony: She seems to be in a relationship with Reddington.
- We Hardly Knew Ye: Though she appears in several episodes, she got very little screen time or development by the time she was killed.
Played By: Fisher Stevens
- Amoral Attorney: He's a highly-desired lawyer for all kinds of criminals, including Red. Oh, and he also wound up in prison himself.
- Jerk with a Heart of Gold: Marvin is irritable, short-tempered and rude. He's still a good man.
- Papa Wolf: He wound up in prison because he abducted his son to save him from an abusive mother.
Played By: Charles BakerA mysterious associate of Reddington.
- The Dragon: Seemed to fill this role for Reddington in general.
- Chekhov's Gunman: He was actually present in the very first scene of the pilot, delivering a briefcase to Reddington. However, his appearance was so minor that most viewers didn't even notice. He later showed up at the hospital, having provided Reddington with the means of escape, and was present at the Angel Station Hotel, interviewing Tom when a Russian defector was assassinated.
- Color Motif: As per his name, he had a thing for grey.
- Face Death with Dignity: Knows that Reddington will kill him for his betrayal, and is sadly resigned to it, and pleads only that it be made to look like an accident for his wife's sake.
- Literal-Minded:Reddington: (on the phone about a painting) Oh, the blue? The blue looks...
- The Mole: He's the mole in Reddington's organization. Fitch flipped him by threatening his family.
- Mysterious Past: While the show has told us Dembe's and Zeng's backstories, Grey remains a complete mystery. Helps that he is still alive...well, until "The Good Samaritan Killer," where Reddington personally executes him for betraying him.
- Number Two: To Reddington.
- Sharp-Dressed Man: Always in a nice suit. And he managed to make Navy fatigues look sharp.
Played by: Lance ReddickReddington's personal investigator when he needs to check on a lead.
- Bounty Hunter: His occupation when he wasn't investigating on behalf of Reddington.
- Brutal Honesty: The Cowboy straight-up tells Reddington he didn't like him.The Cowboy: Well, you want me to bring her in, there's gonna be a fee, and it's gonna cost you double.
Reddington: Oh? Why is that?
The Cowboy: 'Cause I don't like you. And that hat makes your head look funny.
Reddington: The pot meets the kettle at last.
- Character Death: Was executed by Tom Keen after he got too close in his investigation.
- Jerkass: The Cowboy was rather irritable and grumpy. Notably, he's the only associate of Reddington that didn't like him at all.
- Nice Hat: He's known for wearing a wide-brimmed black cowboy hat, hence his nickname.
- No Name Given: His real name was never revealed.
- Only Known by Their Nickname: He's only known as "The Cowboy."
Played By: Bazzel Baz
A Caucasian, white-haired and bearded man who goes with Reddington whenever Dembe is usually not available. He seems to lead a small Special Ops army for Reddington.
- Badass Army: Leads one.
- A Father to His Men: He truly cares for the "soldiers" under his command. He takes it pretty hard when any are killed.
- No Name Given: His name was only mentioned in "The Director: Conclusion".
- Number Two: To Reddington in case Dembe is not around.
- Uncertian Doom: Shot by Mr. Kaplan in the Season 4 finale and is last seen bleeding with an ambulance on the way.
Played By: Hal Ozsan
One of Reddington's mercenaries, who serves as a Cold Sniper. He tails Liz after the death of Agent Malik to make sures she's okay.
- Chekhov's Gunman: He's the one who "accidentally" bumped into Liz at one of her motel residences.
- Cold Sniper: His function with Reddington's group. It's mostly seen when he takes out Dr. Creel with a headshot.
- Friendly Sniper: What he tries to be for Liz. Liz, however, doesn't appreciate it.
- Distracted by the Sexy: The decoy Liz uses this to his advantage so that the actual Liz can sneak out and go to the hidden holding area where she locked up Tom.
- Just Following Orders: The reason Ezra uses when Liz tries to talk him into not tailing her. Liz says the same thing when she sics an FBI SWAT team to arrest him in his motel room.
- Sniping Mission: Ezra's main role after he was ordered to shadow Liz.
- Weapon of Choice: Ezra uses a Desert Tactical Arms Stealth Recon Scout Sniper Rifle.
Played by: Clark MiddletonA diminutive employee of the DMV who works for Reddington as a tracker.
- Badass Bureaucrat: Apparently does most of his work from behind a desk at the DMV, but is a very gifted tracker.
- Bunny-Ears Lawyer: Reddington barely tolerates Glen's constant lies and obnoxious personality, but has plenty of use for his tracking skills.
- Lame Excuse: Apparently tends to throw these out whenever he can't deliver, such as claiming his mother has cancer or that his brother-in-law has Legionnaire's Disease.
- The Napoleon: It takes some pretty serious balls to mouth back at one of the world's most notorious criminals.
- Troll: Gets a big kick out of getting Reddington, or anyone, angry. He works at the DMV for this very reason.
- We Need a Distraction: Helps Liz get critical evidence against her in a station by pretending to have a heart attack.
- Vitriolic Best Buds: He's probably the only character who can consistently annoy and get under Red's skin on a regular basis, and he takes great pleasure in trolling and irritating one of the most dangerous criminals in the world...yet, the two of them have still worked together for several years and clearly have a degree of mutual respect. They border on Sitcom Arch-Nemesis at times, but they both know they can each rely on the other to come through for them...eventually, at least.
Played By: Teddy ColucaAn old man who specializes in enhanced interrogation for Reddington when he's needed. He's always seen with an oxygen tank.
- Bunny-Ears Lawyer: You'd be hard-pressed to find a man with a more esoteric approach to interrogation , but so far he has never failed to break a subject Red gives him.
- He's Back: Shows up again in "Anna-Gracia Duerte", being back in Reddington's employ.
- Noodle Implements: He is always requesting the most bizarre items he needs for his interrogation.
- Screw This, I'm Outta Here!: In "Mr. Kapalan", he decides to leave since he doesn't want to risk getting arrest in the wake of Kaplan turning against Red.
- We Have Ways of Making You Talk/Torture Always Works: Depending on the person Brimley's told to torture. It sometimes works and sometimes, it results in a dead end.
Played by: Dan McCabeBorakove serves as Reddington's man in sifting through data when traditional means of searching evidence do not work. He leads a small team in charge of IT work as well.
- Nerd: Borakove is sporting that look.
- Only Sane Man: What Borakove feels after Reddington asked him to reassembled the shredded documents. See You Have Got to Be Kidding Me! for more details.
- The Reliable One: Reddington relied on him to decipher things that can't be done by physical means. This paid off when Reddington was able to get the needed information on Berlin's faction in "Berlin".
- The Smart Guy: He gets involved in IT duties when Reddington needs him.
- You Have Got to Be Kidding Me!: Borakove when he finds out that Reddington wants him to reassembled shredded clasified documents he and Dembe obtained from the FBI black ops site.Reddington: Put it together.
Borakove: You're kidding right?
Reddington: Borakove, I hate sarcasm and I love puzzles.
Played by: Jack DimichA Czech politician who serves as Reddington's inside man whenever he needs to get something done in the Czech Republic.
- Bilingual Bonus: He speaks fluent Czech and English.
- Clear My Name: What he's doing after he stepped down from Czech politics.
- Frame-Up: What happened to him in "The Kingmaker" courtesy of him.
- Inside Man: Emil serves as this for Reddington in the Czech Republic.
- No Party Given: Emil Dusek's politcal party affiliation is not given.
- Not What It Looks Like: The politician tries to defend himself on television when he was arrested for killing a male escort.
Played by: Jojo GonzalezAn assassin/bagman who helps Reddington snatch persons of interest from the Philippines.